- Design, synthesis, cytotoxic activity, and apoptosis inducing effects of 4- And N-substituted benzoyltaurinamide derivatives
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In this study, a group of 4-substituted benzoyltaurinamide derivatives were designed, synthesized, and investigated for their anticancer activity against three cancer cell lines and one nontumorigenic cell line by MTT assay. Among the final compounds, methoxyphenyl derivatives 14, 15, 16 were found to be effective against all the tested cancerous cell lines with promising selectivity. The most active compounds were further evaluated to determine the molecular mechanism of their anticancer activity by using western blot assay and the Annexin V-FITC/PI test. Compound 14 (in SH-SY5Y and MDA-MB-231 cell lines) and 15 (in SH-SY5Y cell line) were found to induce intrinsic apoptotic pathway by upregulating BAX, caspase-3, and caspase-9, while downregulating Bcl-2 and Bcl-xL expression levels. According to mechanistic studies, compounds displayed their anticancer activity via three different mechanisms: a. caspase-dependent, b. caspase-independent, and c. caspase-dependent pathway that excluded caspase-9 activation. As a result, this study provides interesting data which can be used to design new taurine-based anticancer derivatives.
- Akgül, ?zlem,Erdo?an, Mümin Alper,Birim, Dervi?,Kayaba?i, ?a?la,Gündüz, Cumhur,Arma?an, Güliz
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p. 1674 - 1693
(2021/01/05)
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- A process for preparing 2 - amino-ethyl sulfonamide hydrochloride
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The invention relates to a method for preparing 2-amino ethanesulfonamide hydrochloride. The method comprises the following steps: (1) reacting by virtue of chloroethylsulfonyl chloride with phthalimide potassium salt, so as to prepare N-(2- phthalimide ethyl sulfonyl)phthalimide (intermediate 1); and (2) reacting by virtue of the intermediate 1 with sodium borohydride, so as to prepare 2-aminoethanesulfonamide, and carrying out hydrochloric acid acidification, so as to obtain 2-amino ethanesulfonamide hydrochloride. The method is characterized in that 2-amino ethanesulfonamide hydrochloride is prepared from chloroethylsulfonyl chloride for the first time, a preparation process is simple, and waste liquids such as acetic acid, tetrahydrofuran, dioxane, hydrazine hydrate and phosphorus oxychloride are not produced.
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Paragraph 0023; 0028; 0033; 0037-0038; 0043
(2018/04/26)
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- Method for synthesis of taurideamide hydrochloride (2-aminoethylsulfonamide hydrochloride)
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The present invention discloses a method for synthesis of taurideamide hydrochloride (2-aminoethylsulfonamide hydrochloride) which is an important basic medicinal raw material, the preparation methodof the taurideamide hydrochloride (2-aminoethylsulfonamide hydrochloride) belongs to the field of medicinal chemistry synthesis. Compound (I) (2-bromoethylsulfonyl chloride) is used as a starting material, ammonia is used as a nucleophilic reagent for nucleophilic substitution of chlorine atoms on sulfonyl chloride and bromine atoms on 2-site of ethyl of the compound (I) (2-bromoethylsulfonyl chloride), and the compound (II) taurideamide hydrochloride (2-aminoethylsulfonamide hydrochloride) is formed by action of the compound (I) (2-bromoethylsulfonyl chloride) and hydrochloric acid in ethanol, and a reaction scheme is shown in the specification. The method has the advantages of simple route, simple post-treatment, little side reaction and high yield, and meets the requirements of industrialized production.
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Paragraph 0032; 0057
(2018/04/02)
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- Preparation method of taurylamine hydrochloride
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The invention discloses a preparation method of taurylamine hydrochloride. The preparation method comprises the following steps: by using taurine as an initial raw material, sequentially carrying out amino protecting reaction, chlorination reaction, ammonolysis reaction and deprotection-salification to obtain the taurylamine hydrochloride. The amino protecting group adopted by the amino protecting reaction is benzyl chloroformate, and the amino protecting group is carried out at 5-15 DEG C in the presence of sodium hydroxide and water. The chlorination reagent adopted by the chlorination reaction is thionyl chloride, and the chlorination reaction temperature is 60-70 DEG C. The ammonolysis reaction is carried out in tetrahydrofuran under the action of stronger ammonia water, and the ammonolysis reaction temperature is 5-15 DEG C. The total yield of the four-step reaction can reach 80% or above, the product purity can reach 99% or above, and thus, the method is suitable for industrialized mass production.
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Paragraph 0031; 0032; 0033; 0034; 0035
(2017/01/02)
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- An Unusual Natural Product Primary Sulfonamide: Synthesis, Carbonic Anhydrase Inhibition, and Protein X-ray Structures of Psammaplin C
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Psammaplin C is one of only two described natural product primary sulfonamides. Here we report the synthesis of psammaplin C and evaluate the inhibition profile against therapeutically relevant carbonic anhydrase (CA) zinc metalloenzymes. The compound exhibited unprecedented inhibition of an important cancer-associated isozyme, hCA XII, with a Ki of 0.79 nM. The compound also displayed good isoform selectivity for hCA XII over other CAs. We present the first reported protein X-ray crystal structures of psammaplin C in complex with human CAs. We engineered the easily crystallized hCA II enzyme to mimic both the hCA IX and hCA XII binding sites and then utilized protein X-ray crystallography to determine the binding pose of psammaplin C within the hCA II, hCA IX, and hCA XII mimic active sites, all to high resolution. This is the first time a natural product primary sulfonamide inhibitor has been assessed for inhibition and binding to CAs.
- Mujumdar, Prashant,Teruya, Kanae,Tonissen, Kathryn F.,Vullo, Daniela,Supuran, Claudiu T.,Peat, Thomas S.,Poulsen, Sally-Ann
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supporting information
p. 5462 - 5470
(2016/07/06)
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- Synthesis and antiviral, insecticidal, and fungicidal activities of gossypol derivatives containing alkylimine, oxime or hydrazine moiety
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Gossypol is a part of the cotton plant's defense system against pathogens and herbivorous insects. To discover gossypol analogs with broad spectrum and high activity, a series of gossypol alkylamine Schiff base, oxime and hydrazone derivatives were synthesised and bioassayed. The biological results indicated that most of these derivatives exhibited higher anti-TMV activity than gossypol. Interestingly, the activities of compounds 10, 15, 18, 20, 23 and 26 were much higher than that of ribavirin. Furthermore, compound 26, which was low toxicity to rat, showed better activity than control plant virus inhibitors in the field. Additionally, allyl amine Schiff base (9) displayed remarkable insecticidal activities against Mythimna separata, Helicoverpa armigera and Ostrinia nubilalis, whereas (pyridin-3-yl)methanamine Schiff base (13) showed excellent activity against Culex pipiens pallens. The fungicidal results revealed that all of compounds exhibited good activity against Physalospora piricola.
- Li, Ling,Li, Zheng,Wang, Kailiang,Liu, Yuxiu,Li, Yongqiang,Wang, Qingmin
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p. 474 - 483
(2016/01/25)
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- ESTRA-1,3,5(10),16-TETRAENE-3-CARBOXAMIDES FOR INHIBITION OF 17Β-HYDROXYSTEROID DEHYDROGENASE (AKR1 C3)
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The invention relates to AKR1C3 inhibitors of formula (I) and to processes for preparation thereof, to the use thereof for treatment and/or prophylaxis of diseases and to the use thereof for production of medicaments for treatment and/or prophylaxis of diseases, especially of bleeding disorders and endometriosis.
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- 4-(SUBSTITUTED ANILINO)QUINAZOLINE DERIVATIVES AS TYROSINE KINASE INHIBITORS
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The present invention relates to 4-(substituted anilino)-quinazoline derivatives as tyrosine kinase inhibitors. Specifically, compounds of formula I, or pharmaceutically acceptable salts or solvates thereof are disclosed, in which each substitutent in formula I is defined in the description. Preparation method of the compounds of formula I, pharmaceutical compositons and pharmaceutical uses thereof are also disclosed. The compounds of formula I are effective tyrosine kinase inhibitors.
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Page/Page column 15
(2012/08/14)
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- 4-(Substituted Anilino)-Quinazoline Derivatives Useful as Tyrosine Kinase Inhibitors
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The present invention relates to 4-(substituted anilino)-quinazoline derivatives as tyrosine kinase inhibitors. Specifically, compounds of formula I, or pharmaceutically acceptable salts or solvates thereof are disclosed, in which each substitutent in formula I is defined in the description. Preparation method of the compounds of formula I, pharmaceutical compositions and pharmaceutical uses thereof are also disclosed. The compounds of formula I are effective tyrosine kinase inhibitors.
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Page/Page column 10
(2012/08/28)
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- Quinazolines and related heterocyclic compounds and their therapeutic use
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A compound of the formula wherein X is CR1 or N; Y is CR3 or N; R1, R3, R4, R5 and R6 are independently H, F, Cl, Br, I, or a hydrocarbon group which optionally contains one or more heteroatoms; R7 is a heterocyclic group including one or more N atoms; R' is Rx or NRyRz wherein Rx, Ry and Rz are each H or the same or different groups, including cyclic groups formed by Ry and Rz with the N atom, of up to 20 C atoms and optionally including up to 3 further heteroatoms selected from N, O and S; or a pharmaceutically acceptable salt, ester or solvate thereof, has therapeutic utility.
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Page/Page column 15-16
(2009/07/18)
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